There’s nothing quite like summer in Chicago. All season long, you can play beach volleyball on the sandy shores of Lake Michigan, kayak through a skyscraper canyon, sip cocktails from rooftop bars with city views, hit up free outdoor music festivals featuring everything from blues to jazz to gospel — the list goes on and on. Here’s your guide to making the most out of summer in Chicago.
Hit the beach
Chicago is blessed with miles and miles of sandy lakefront beaches. Build a sandcastle empire at Foster Beach, cool off at trendy Shore Club Chicago (where you can reserve a daybed or a cabana) at North Avenue Beach, or simply enjoy the view (and catch a beach volleyball game) at Oak Street Beach. If you’re a bit of a thrill-seeker, you can rent a jet ski, kayak, paddleboard, or fly board at Chicago Water Sport Rentals at 31st Street Harbor.
It’s virtually impossible to provide a shortlist of great outdoor dining spots in the city, but we’ll try.
- Check our outdoor dining guide for patios and rooftops open now
- Want to dine with a view? Explore beachfront restaurants
- Or discover all the restaurants on the Chicago Riverwalk
Or just stroll through any neighborhood in Chicago, and you’ll have plenty of stellar alfresco spots to choose from.
Take a boat cruise
Each summer, Chicago’s many boat cruises set sail on Lake Michigan and the Chicago River. There’s tons of different Chicago cruise options for a variety of interests, from leisurely dinner cruises to educational architecture tours to high-speed thrill rides.
Hop on a Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady to soak up the sun while learning about the city’s historic buildings. Or get your heart pumping on a fast-paced Seadog Cruise. Island Party Hut brings the tiki vibes, while Odyssey offers a more refined experience.
Get out on the water
Chicago is home to two stunning waterfronts — Lake Michigan, with miles of sandy shoreline, and the Chicago River, a skyscraper canyon through the heart of the city. And both offer plenty of opportunities to get out on the water. You can rent jet skis and paddleboards on the lakefront and kayaks on the river and lake. You can also rent all types of boats, from small electric vessels to pontoon party boats, on the lake and river.
See Navy Pier
See the sights along Navy Pier, one of the city’s most popular attractions. Here’s just a sample of the many things to see and do there this summer:
- Hop on a lakefront cruise
- Dine at outdoor restaurants
- Enjoy a classic Rainbow Cone
- Check out a live DJ set
- Enjoy the waterfront beer garden
- Order a margarita to go as you walk the Pier
- Rent a bike or take a bike tour
- Check out the country’s largest rooftop bar
Explore a city park
The Chicago Park District oversees more than 600 parks, with open space in just about every corner of the city. Millennium Park’s free Lurie Garden is an urban oasis in the heart of the Loop. Also nearby, you can let the kids climb, skate, and play at the sprawling Maggie Daley Park. Head to our neighborhoods for even more green space — work up a sweat with a bike ride or jog along The 606, take in lakefront views at the 31st Street Beach, and meander down the boardwalk at Lincoln Park’s South Pond.
Head to a rooftop
Chicago’s skyline is filled with rooftop bars and restaurants, perfect for cocktails and bites on a sunny afternoon or warm summer’s evening. One local favorite is LH Rooftop, which wows with the city’s only tri-level rooftop lounge overlooking the Chicago River. Set in a 1920s-era Art Deco skyscraper, Aire at the Hyatt Centric The Loop Chicago mixes urban rooftop lounging with handcrafted cocktails and open-air panoramic views, while the Renaissance Chicago Downtown Hotel’s Raised Bar offers fire pits, plenty of seating, and local beers on tap.
Join a tour
A tour is one of the best ways to make the most of your Chicago visit. Learn about the city’s iconic architecture with Free Tours by Foot, Inside Chicago Walking Tours, and Chicago Detours walking tours. Or see the city on two wheels via a bike or Segway tour with Bike and Roll Chicago or Bobby’s Bike Hike. You can also explore Chicago’s unique neighborhoods with a friendly local for free through Chicago Greeter Tours.
Fall in love with public art
Public art in Chicago is splashed on surfaces all around the city: it covers train stations, rises tall on downtown skyscrapers, and pops up on sidewalks, in office lobbies, and along the lakefront. Discover works of public art in the Loop by masters such as Picasso and Chagall, check out neighborhood street art, or see international street artists make their mark on districts like the Wabash Arts Corridor. Take a public art tour, or create your own. Either way, get your camera ready, and start Instagramming!
Hear music at a museum
Head to the Shedd Aquarium for Jazzin’ at the Shedd every Wednesday night this August. The evening features live tunes from a top Chicago jazz ensemble, sweeping views of the city skyline, and open access to the Shedd’s many immersive exhibits.
Throughout the summer, the Museum of Contemporary Art hosts Tuesdays on the Terrace, an evening of free music on the MCA’s scenic terrace. This annual summer performance series highlights artists from Chicago’s internationally renowned jazz community.
Note: Stay tuned for more information about Chicago festivals in 2021!
Get your fest on
Summer weekends in Chicago are brimming with street fairs and festivals. Just about every neighborhood hosts one, and you’ll be guaranteed to find stand-out food and drink while you’re there. Some highlights: Ribfest in North Center, where you can sample dozens of different barbecued ribs; Taste of Chicago, which spotlights the city’s world-class restaurant scene; the Renegade Craft Fair, which takes over Division Street with wares from hundreds of artisans; and Pride Month events like Pride in the Park celebrating Chicago’s vibrant LGBTQ+ culture. Also, Chicago hosts a variety of craft beer festivals throughout the year, showcasing our dynamic brewing scene.
Jam out, outside
The sound of music festivals fills Chicago in the summer. Find a sun-soaked patch of grass and enjoy the free concert season at Jay Pritzker Pavilion in Millennium Park. Or slather on the sunscreen and take part in one of the city’s massive summer music festivals, like the all-star lineups at Lollapalooza and Pitchfork; annual multi-day freebies like the Chicago Blues Festival; and the latest country hits at Windy City Smokeout.
Catch a movie under the stars
The Millennium Park free summer film series is screened under the stars at the iconic Jay Pritzker Pavilion on Tuesdays from June through August. Guests take a seat at the Pavilion or lounge on the Great Lawn with a picnic as both old favorite and new blockbusters are presented on a state-of-the-art, 40-foot LED screen.
Save up to 55% admissions to Chicago’s top attractions with Go Chicago. Explore Chicago at your own pace. Pay nothing at the gate — just use the pass on your phone or print it out in advance. No need to exchange money or hand over a credit card with contactless scanning at the attraction. The interactive mobile app will have you traveling around the city like a local! Choose from 25+ attractions, including:
- Skydeck Chicago
- Shoreline Architecture River Cruise
- Hop-On Hop-Off Big Bus Tour
- Art Institute of Chicago
- Navy Pier rides
- And so much more!
Explore Go Chicago options:
Get your Chicago CityPASS!
Planning a future trip to Chicago? Experience the city’s famous attractions at a 50% savings with Chicago CityPASS. Take your time and enjoy each attraction with 9 consecutive days to use your tickets. And, with convenient mobile tickets and prepaid admission, you’ll get to skip select lines. Rest assured that should your plans change, you’re covered by flexible 365-day risk-free returns. Trusted by 23 million travelers for 23 years.
Includes prepaid admission to 5 must-see attractions:
- Shedd Aquarium
- Skydeck Chicago
- Field Museum
- Adler Planetarium OR Art Institute of Chicago
- Museum of Science and Industry, Chicago, OR 360 CHICAGO Observation Deck
Spend less, experience more. Learn more.